1-(5-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid → 5-Methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylic acid
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=[N:9]2)=[N:6][CH:7]=1>CN(C)C=O.[C].[Pd]>[CH3:13][C:12]1[N:8]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=2)[N:9]=[CH:10][C:11]=1[C:14]([OH:16])=[O:15]Participants
4
Procedure
To a solution of 1-(5-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid (30 mg) described in Reference Example 24 in N,N-dimethylformamide (1 ml) was added 10% palladium carbon (containing about 50% water) (10 mg) at room temperature, and stirred at the same temperature for 30 minutes under hydrogen atmosphere. After completion of the reaction, the reaction solution was filtered through Celite, then the solvent was evaporated in vacuo, azeotropically concentrated together with toluene to give the titled compound (23 mg) as a white solid.
Workup
- customAfter completion of the reaction
- filtrationthe reaction solution was filtered through Celite
- customthe solvent was evaporated in vacuo
- concentrationazeotropically concentrated together with toluene
Sources & evidence
- ORD record
- ord-3282666ea7814e558169ab2525ffbf40
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150555B2
Reaction notes
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